Water → HCID 10267910, compound

HRID 2121626Notes

Reaction equation

[CH3:1][C:2]1[O:3][C:4]([C:13]2[CH:14]=[CH:15][C:16]([NH:19][NH:20][C:21](=O)[CH:22]([CH3:24])[CH3:23])=[N:17][CH:18]=2)=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.O.[OH-].[Na+]>P(Cl)(Cl)(Cl)=O>[CH:22]([C:21]1[N:17]2[CH:18]=[C:13]([C:4]3[O:3][C:2]([CH3:1])=[N:6][C:5]=3[C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:14]=[CH:15][C:16]2=[N:19][N:20]=1)([CH3:24])[CH3:23]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 23 mg of isobutyric acid N′-[5-(2-methyl-4-phenyl-oxazol-5-yl)-pyridin-2-yl]-hydrazide in 0.68 mL of phosphorous oxychloride was heated at 60° C. for 16 hours. The mixture was cooled to 22° C. and carefully added to 25 mL of water. The aqueous mixture was made basic with 3 N sodium hydroxide and extracted with ethyl acetate (3×). The combined extracts were washed with brine, dried (sodium sulfate), filtered, and the filtrate was concentrated to a dark yellow oil. This oil was purified by flash chromatography (eluting with 97:3 ethyl acetate/methanol) to give 14 mg of 3-isopropyl-6-(2-methyl-4-phenyl-oxazol-5-yl)-[1,2,4]triazolo[4,3-a]pyridine as a light yellow solid. LCMS (m/z) 319 M+1. 1H NMR (400 MHz, CDCl3 δ8.18 (s, 1 H), 7.85 (d, 1 H, J=9.8 Hz), 7.60-7.62 (m, 2 H), 7.42-7.49 (m, 4 H), 3.32-3.34 (m, 1 H), 2.63 (s, 3 H), 1.51 (d, 6 H, J=6.7 Hz).

Workup

temperatureThe mixture was cooled to 22° C.
extractionextracted with ethyl acetate (3×)
washThe combined extracts were washed with brine
dry with materialdried (sodium sulfate)
filtrationfiltered
concentrationthe filtrate was concentrated to a dark yellow oil
customThis oil was purified by flash chromatography (eluting with 97:3 ethyl acetate/methanol)

Sources & evidence

ORD record: ord-67913d9c733e4bc48628121999305641
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06696464B2

Reaction notes

Loading…